The Golden Years Are a Lie—And I'm Done Pretending Otherwise

Why I'm bringing my retirement dreams into my 40s (and what watching my parents' generation taught me about waiting)

I've been thinking about tombstones lately.

Not in a morbid way—more like a clarity exercise. If my entire life had to be boiled down to a single sentence carved in stone, what would I want it to say? After a lot of consideration, I've landed on this: "Now that bitch knew how to live!"

(And yes, I plan to be cremated, so the whole tombstone thing is theoretical. But the sentiment stands.)

What does that sentence mean to me? Well if folks are saying that about me after I’m gone, it means that I never settled for living the life that others expected me to live. I wasn’t afraid to try new things, or go after goals that mattered to me. And the bitch part? That just means that I didn’t take shit from anyone along the way.

So what sparked this meditation on mortality and meaning? Well, I'm a few years shy of 50, which means I've had a front-row seat to watch my parents' entire generation navigate retirement. And what I've observed has fundamentally changed how I think about building a life worth living.

The Golden Years Fallacy

The conventional wisdom goes something like this: Work really, really hard so you can save for retirement. Sacrifice your best years building a nest egg so that in your golden years, you can finally ride off into the sunset and do all the things you've been dreaming about.

It sounds reasonable. Responsible, even.

But I’ve watched too many people cross that finish line only to find the dream was a mirage. They discovered that those grand travel plans are harder to swing on a fixed income without company benefits. The hobbies they fantasized about for years—hiking, kayaking, exploring new cities—are a lot easier on the body at 45 than at 75. And most painfully, I've seen health issues appear unexpectedly, changing everything in an instant.

The reality for many is that retirement looks a lot like their pre-retirement life, just with less income and more doctor's appointments. It’s not the adventure they were promised. And it’s definitely not the life I want for myself.

My Philosophical Guides

This realization sent me searching for a different way to think. I’ve always loved philosophy, and a book that genuinely changed my life is Alan Watts’ The Wisdom of Insecurity. The core message: if you spend your life perpetually thinking about the past or building for the future, you're always missing the only thing that’s real—right now.

But my other great philosophical guide is a little less traditional: Ferris Bueller

I know that sounds ridiculous, but hear me out. That movie was supposedly made for teenagers, yet it always felt to me like the story of someone going through a midlife crisis, just told through the voice of a 17-year-old. "Life moves pretty fast. If you don't stop and look around once in a while, you could miss it." That's not typical teenager wisdom—that's something you usually don't grasp until much later in life.

Now Ferris is definitely a flawed character - he’s cocky, selfish and unperturbed by consequences - but I suppose, what teenager isn’t. But what I love about him is the way he makes the most of his unearned confidence and his ability to live in the moment. He knows exactly what the consequences are if he gets caught, but while every other high school student is just trying to get through the school year, he's focused on the present reality that his childhood is about to end, his best friend is going to move away, and he willing to take risks in order to hold on to this moment as long as possible.

The most famous scene in the movie is when he charms his way onto a parade float and sings to a very enthusiastic crowd. It’s memorable because it’s audacious. He didn’t have the credentials to be up there, but he did it anyway and he was celebrated for it. Audiences love that scene because deep down we all want the courage to truly live in the present tense.

So I started asking myself: what would it look like to live with that kind of present-tense courage, minus the teenage recklessness?

The Real Cost of Waiting

We're constantly told that the biggest risk to our future selves is not saving enough money for retirement. But I think we've got it backwards. The real risk isn't running out of money—it's running out of time, energy, and health. You can always find ways to make more money if you need to, but when your time is up, it's up. That's what the conventional "work now, live later" model actually costs us: the irreplaceable present moment, and the physical and mental capacity to fully live in it.

But there’s another hidden cost to putting everything off. The idea of "someday" keeps our dreams vague and fuzzy. It’s easy to say, “I’ll travel when I retire.” It’s much harder to answer the real questions: Where do I want to live? What activities do I want to do? Who do I want to spend time with?

Getting crystal clear on these questions has been a game-changer for me. It’s transformed my hazy fantasy into a concrete goal I can start moving toward now, instead of treating "someday" like a magical date when life begins.

My Experiment in Present-Tense Living

So, what does this look like in practice? I still run my business strategy consulting firm, but I’ve started building a creative business on the side, licensing my illustrations. I don't expect it to replace my consulting income, but it's work I love, and the goal is to create a stream of revenue that can fund more of our "someday" adventures while I gradually scale back my other work.

And my husband and I are done waiting. Our kids are teenagers now, old enough to be left on their own for a bit. I’ve always dreamed of visiting Singapore, so we booked a week-long trip for this fall.

It’s a small step, but it feels like we’re reclaiming control, pulling a piece of our future into the present.

Let's Talk About the Money

I know what some of you are thinking: "That's irresponsible. What about security? You should be maxing out your retirement savings. You can't count on art to pay the bills."

Believe me, my husband and I have had this conversation. We've always been frugal. We live in a modest house and drive our cars until they give out. But at a certain point, you have to ask yourself: how much is enough? Once you have a solid foundation, does it make sense to keep hoarding resources for a future that’s not guaranteed, at the expense of the life you have today?

This shift might mean we downsize our home earlier than planned or make other trade-offs down the line. But those are trade-offs we're willing to make to build a life we love.

The Agency Most People Don't Realize They Have

I recognize that even having conversations about these kinds of choices comes from a place of privilege. Not everyone has the luxury of choice I'm describing. But I also think most people have more agency than they give themselves credit for.

The point isn't that my way is the right way. It’s about consciously designing your own life. It starts with asking what you truly want and then looking honestly at the trade-offs you’re willing to make to get there. It’s about giving yourself permission to question the timeline and assumptions you’ve been handed.

As one of my other favorite philosophers, Henry David Thoreau, said “ Go confidently in the direction of your dreams. Live the life you've imagined”

A Different Kind of Finish Line

So at age 47, I’m taking day trips by ferry to nearby islands for lunch, and I’m spending a little less time behind my keyboard and a little more catching up with friends.

And in a few years, when my kids are in college, I’ll travel more while continuing to consult and illustrate. So that by the time my body forces me to slow down, I'll be ready and happy to do so—because I'll have been living intentionally all along.

Alan Watts and Ferris Bueller were right. The only moment we’re truly guaranteed is this one.

So, how are you going to spend it?

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